[2,7-Dihy­droxy-8-(4-phen­oxy­benzo­yl)naphthalen-1-yl](4-phen­oxy­phen­yl)methanone

Hijikata, D.; Sasagawa, K.; Yoshiwaka, S.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536812052038

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Pages o208-o209

doi:10.1107/S1600536812052038

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[2,7-Dihydroxy-8-(4-phenoxybenzoyl)naphthalen-1-yl](4-phenoxyphenyl)methanone

Daichi Hijikata,^a Kosuke Sasagawa,^a Sayaka Yoshiwaka,^a Akiko Okamoto ^a ^* and Noriyuki Yonezawa ^a

^aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology (TUAT), Koganei, Tokyo 184.8588, Japan
^*Correspondence e-mail: aokamoto@cc.tuat.ac.jp

(Received 8 December 2012; accepted 29 December 2012; online 9 January 2013)

In the title compound, C₃₆H₂₄O₆, the benzoyl groups at the 1- and 8-positions of the naphthalene system are in an anti orientation. Both carbonyl groups form intramolecular O—H⋯O hydrogen bonds with hydroxy groups affording six-membered rings. The benzene rings of the benzoyl groups make dihedral angles of 59.26 (13) and 59.09 (13)° with the naphthalene ring system. Zigzag C—H⋯O chains and ladder C—H⋯O chains between the phenoxybenzoyl groups along the ab diagonals form an undulating checkered sheet. The molecules are further connected into a three-dimensional network by C—H⋯π interactions.

Related literature

For electrophilic aromatic aroylation of the naphthalene core, see: Okamoto & Yonezawa (2009 ); Okamoto et al. (2011 , 2013 ). For the structures of (2,7-dimethoxynaphthalene-1,8-diyl)bis(4-fluorophenyl)dimethanone and 2,7-dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene, see: Watanabe et al. (2010 ) andr Hijikata et al. (2010 ), respectively.

Experimental

Crystal data

C₃₆H₂₄O₆
M_r = 552.55
Monoclinic, C c
a = 16.0313 (3) Å
b = 18.4956 (3) Å
c = 12.1238 (2) Å
β = 131.389 (1)°
V = 2696.95 (9) Å³
Z = 4
Cu Kα radiation
μ = 0.75 mm⁻¹
T = 193 K
0.60 × 0.55 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.661, T_max = 0.929
22236 measured reflections
4868 independent reflections
4527 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.096
S = 1.08
4868 reflections
382 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 2389 Friedel pairs
Flack parameter: 0.05 (19)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C25—C30 and C31—C36 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O1	0.84	1.83	2.560 (3)	145
O6—H6A⋯O2	0.84	1.88	2.563 (3)	138
C26—H26⋯O4ⁱ	0.95	2.48	3.377 (4)	157
C27—H27⋯O1ⁱ	0.95	2.51	3.269 (4)	137
C32—H32⋯O3ⁱⁱ	0.95	2.49	3.382 (4)	156
C33—H33⋯O2ⁱⁱ	0.95	2.51	3.270 (4)	137
C14—H14⋯Cg1ⁱⁱⁱ	0.95	2.80	3.740 (2)	171
C21—H21⋯Cg2^iv	0.95	2.80	3.740 (2)	171
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[x, -y, z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812052038/rn2112sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812052038/rn2112Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812052038/rn2112Isup3.cml

checkCIF report

Comment top

In the course of our study on electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have proven to be formed regioselectively with the aid of suitable acidic mediators (Okamoto & Yonezawa, 2009; Okamoto et al., 2011). As one of the applications of peri-aroylnaphthalene synthetic studies, the authors have integrated the resulting molecular unit to the poly(ether ketone) backbone via nucleophilic aromatic substitution polycondensation (Okamoto et al., 2013). The poly(ether ketone)s composed of 1,8-diaroylenenaphthalene units show unique thermal properties and solubility for organic solvents. These notable properties could arise from the structural features of the 1,8-diaroylene naphthalene units. Under these circumstances, the authors have undertaken the X-ray crystal structural study of several 1,8-diaroylated naphthalene analogues exemplified by (2,7-dimethoxynaphthalene-1,8-diyl)bis(4-fluorophenyl)dimethanone (Watanabe et al., 2010) and 2,7-dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene (Hijikata et al., 2010). These molecules have essentially the same non-coplanar features. The two aroyl groups are twisted so they are almost perpendicular to the naphthalene rings.

The molecular structure of the title compound is displayed in Fig. 1. Two benzoyl groups are on the 1,8-positions of the naphthalene ring and are in an anti orientation relative to one another. The benzene rings of the benzoyl groups make dihedral angles with the naphthalene ring of 59.26 (13) and 59.09 (13)°, respectively. The dihedral angles between the benzene rings of the benzoyl groups and those of the phenoxy groups are 69.05 (13) and 69.02 (13)°. Both carbonyl groups form intramolecular O—H···O hydrogen bonds with hydroxy groups affording six-membered rings. (Fig. 1, Table 1).

In the crystal structure, the molecular packing of the title compound is stabilized mainly by C—H···O and C—H···π interactions. The aromatic hydrogen atoms of the phenoxy groups form two types of intermolecular C—H···O interactions with the ethereal oxygen atom of the phenoxy groups(C26—H26···O4ⁱ= 2.48 Å, C32—H32···O3ⁱⁱ= 2.49 Å; Fig. 2 and Table 1) and the carbonyl oxygen atom (C27—H27···O1ⁱ= 2.51 Å, C33—H33···O2ⁱⁱ= 2.51 Å; Fig. 2 and Table 1). Intermolecular C—H···π interactions between the aromatic hydrogen atom of the benzoyl group and the centroid of the benzene ring of the phenoxy group (C14—H14···Cg1ⁱⁱⁱ= 2.80 Å, C21—H21···Cg2^iv= 2.80 Å; Fig. 3 and Table 1) are observed.

Related literature top

For electrophilic aromatic aroylation of the naphthalene core, see: Okamoto & Yonezawa (2009); Okamoto et al. (2011, 2013). For the structures of the closely related compounds (2,7-dimethoxynaphthalene-1,8-diyl)bis(4-fluorophenyl)dimethanone and 2,7-dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene, see: Watanabe et al. (2010) andr Hijikata et al. (2010), respectively.

Experimental top

To a stirring solution of 1,8-bis(4-phenoxybenzoyl)-2,7-dimethoxynaphthalene (1.0 mmol, 580 mg) in dichloromethane (1.0 ml) at 0°C was added 1.0 M boron tribromide solution in dichloromethane (4.4 ml) slowly, and the reaction mixture was allowed to reach the room temperature. After the reaction mixture had been stirred at room temperature for 48 h, the reaction mixture was cooled to 0 ^oC and very slowly quenched with water and extracted with CHCl₃. The organic layer thus obtained was dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give a cake. The crude product was purified by column chromatography (silica gel, CHCl₃) to give the title compound (isolated yield 88%). Single crystals suitable for X-ray diffraction were obtained by crystallization from Et₂O-hexane (v/v = 1:2).

¹H NMR δ (300 MHz, CDCl₃): 6.82–6.84 (4H, m), 7.08–7.26 (10H, m), 7.40 (4H, t, J=7.9 Hz) 7.86 (2H, d, J=8.9 Hz), 11.29 (2H, s) p.p.m.

¹³C NMR δ (75 MHz, CDCl₃): 115.13, 117.03, 117.28, 120.02, 122.02, 124.46, 130.00, 130.68, 133.79, 136.09, 155.58, 161.74, 195.80 p.p.m.

IR (KBr): 3396(O—H), 1620 (C=O), 1608, 1583, 1487 (Ar, naphthalene) cm^-1.

HRMS (m/z): [M + H]⁺ calcd for C₃₆H₂₅O₆, 553.1651 found, 553.1637.

m.p. 464.6–465.9 K.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: Il Milione (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of title compound, showing 30% probability displacement ellipsoids. The intramolecular O—H···O hydrogen bond is shown as a dashed line.
	Fig. 2. A partial crystal packing diagram of title compound. The intermolecular C—H···O interactions are shown as dashed lines.
	Fig. 3. A partial crystal packing diagram of title compound. The intermolecular C—H···π interactions are shown as dashed lines.

[2,7-Dihydroxy-8-(4-phenoxybenzoyl)naphthalen-1-yl](4-phenoxyphenyl)methanone top

Crystal data top

C₃₆H₂₄O₆	F(000) = 1152
M_r = 552.55	D_x = 1.361 Mg m⁻³
Monoclinic, Cc	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: C -2yc	Cell parameters from 14515 reflections
a = 16.0313 (3) Å	θ = 4.4–68.1°
b = 18.4956 (3) Å	µ = 0.75 mm⁻¹
c = 12.1238 (2) Å	T = 193 K
β = 131.389 (1)°	Block, yellow
V = 2696.95 (9) Å³	0.60 × 0.55 × 0.10 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4868 independent reflections
Radiation source: rotating anode	4527 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 10.000 pixels mm^-1	θ_max = 68.1°, θ_min = 4.4°
ω scans	h = −19→19
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −22→22
T_min = 0.661, T_max = 0.929	l = −14→14
22236 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0414P)² + 1.2872P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.096	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.20 e Å⁻³
4868 reflections	Δρ_min = −0.21 e Å⁻³
382 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.00222 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2389 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.05 (19)

Crystal data top

C₃₆H₂₄O₆	V = 2696.95 (9) Å³
M_r = 552.55	Z = 4
Monoclinic, Cc	Cu Kα radiation
a = 16.0313 (3) Å	µ = 0.75 mm⁻¹
b = 18.4956 (3) Å	T = 193 K
c = 12.1238 (2) Å	0.60 × 0.55 × 0.10 mm
β = 131.389 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4868 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	4527 reflections with I > 2σ(I)
T_min = 0.661, T_max = 0.929	R_int = 0.033
22236 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.096	Δρ_max = 0.20 e Å⁻³
S = 1.08	Δρ_min = −0.21 e Å⁻³
4868 reflections	Absolute structure: Flack (1983), 2389 Friedel pairs
382 parameters	Absolute structure parameter: 0.05 (19)
2 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.46616 (15)	0.24827 (8)	0.4776 (2)	0.0586 (5)
O2	0.36810 (15)	0.00189 (8)	0.4778 (2)	0.0589 (5)
O3	0.78626 (13)	−0.00972 (9)	0.69269 (17)	0.0540 (4)
O4	0.26329 (13)	0.25987 (9)	0.69275 (17)	0.0540 (4)
O5	0.3598 (2)	0.31569 (12)	0.2334 (3)	0.0889 (7)
H5A	0.4028	0.3117	0.3252	0.107*
O6	0.2301 (2)	−0.06560 (12)	0.2333 (3)	0.0887 (7)
H6A	0.2881	−0.0652	0.3226	0.106*
C1	0.33277 (19)	0.18893 (13)	0.2506 (2)	0.0461 (5)
C2	0.3049 (3)	0.25255 (17)	0.1699 (3)	0.0664 (8)
C3	0.2213 (3)	0.2516 (3)	0.0165 (4)	0.0985 (15)
H3	0.2020	0.2950	−0.0374	0.118*
C4	0.1684 (3)	0.1906 (3)	−0.0546 (3)	0.1016 (16)
H4	0.1154	0.1909	−0.1591	0.122*
C5	0.1337 (2)	0.0591 (3)	−0.0547 (3)	0.1027 (16)
H5	0.0822	0.0587	−0.1592	0.123*
C6	0.1529 (3)	−0.0033 (3)	0.0189 (4)	0.1012 (15)
H6	0.1190	−0.0471	−0.0339	0.121*
C7	0.2216 (2)	−0.00274 (17)	0.1702 (3)	0.0661 (8)
C8	0.27453 (17)	0.06111 (13)	0.2507 (2)	0.0460 (5)
C9	0.26698 (17)	0.12502 (15)	0.1775 (2)	0.0487 (5)
C10	0.1889 (2)	0.1250 (2)	0.0211 (3)	0.0757 (9)
C11	0.43775 (19)	0.19208 (11)	0.4067 (2)	0.0426 (5)
C12	0.51884 (16)	0.13161 (11)	0.4748 (2)	0.0369 (4)
C13	0.59891 (17)	0.12824 (12)	0.6275 (2)	0.0422 (5)
H13	0.5936	0.1599	0.6843	0.051*
C14	0.68556 (17)	0.07991 (13)	0.6977 (2)	0.0452 (5)
H14	0.7375	0.0764	0.8019	0.054*
C15	0.69610 (16)	0.03646 (11)	0.6145 (2)	0.0399 (4)
C16	0.61693 (17)	0.03743 (12)	0.4626 (2)	0.0413 (5)
H16	0.6240	0.0065	0.4066	0.050*
C17	0.52707 (17)	0.08406 (12)	0.3929 (2)	0.0405 (5)
H17	0.4707	0.0836	0.2888	0.049*
C18	0.32565 (17)	0.05816 (11)	0.4067 (2)	0.0427 (5)
C19	0.31261 (16)	0.11833 (11)	0.4748 (2)	0.0368 (4)
C20	0.38516 (17)	0.12173 (12)	0.6276 (2)	0.0421 (5)
H20	0.4471	0.0899	0.6844	0.050*
C21	0.36894 (18)	0.17017 (13)	0.6976 (2)	0.0458 (5)
H21	0.4215	0.1738	0.8018	0.055*
C22	0.27547 (17)	0.21371 (11)	0.6151 (2)	0.0399 (4)
C23	0.20247 (17)	0.21294 (12)	0.4623 (2)	0.0412 (5)
H23	0.1397	0.2441	0.4063	0.049*
C24	0.22251 (17)	0.16599 (12)	0.3928 (2)	0.0402 (5)
H24	0.1746	0.1662	0.2886	0.048*
C25	0.83934 (16)	−0.02601 (13)	0.6401 (2)	0.0449 (5)
C26	0.87387 (19)	−0.09629 (14)	0.6575 (3)	0.0530 (6)
H26	0.8565	−0.1317	0.6964	0.064*
C27	0.9345 (2)	−0.11477 (15)	0.6174 (3)	0.0567 (6)
H27	0.9577	−0.1634	0.6274	0.068*
C28	0.9614 (2)	−0.06375 (15)	0.5636 (3)	0.0553 (6)
H28	1.0036	−0.0769	0.5372	0.066*
C29	0.92693 (19)	0.00719 (15)	0.5477 (3)	0.0532 (6)
H29	0.9457	0.0428	0.5108	0.064*
C30	0.86529 (18)	0.02621 (13)	0.5855 (2)	0.0480 (5)
H30	0.8410	0.0747	0.5740	0.058*
C31	0.15740 (18)	0.27605 (13)	0.6400 (2)	0.0447 (5)
C32	0.1402 (2)	0.34624 (14)	0.6574 (3)	0.0536 (6)
H32	0.1966	0.3815	0.6966	0.064*
C33	0.0399 (2)	0.36505 (15)	0.6174 (3)	0.0565 (6)
H33	0.0268	0.4137	0.6274	0.068*
C34	−0.0414 (2)	0.31361 (15)	0.5632 (3)	0.0553 (6)
H34	−0.1098	0.3267	0.5370	0.066*
C35	−0.0229 (2)	0.24338 (15)	0.5473 (3)	0.0536 (6)
H35	−0.0788	0.2079	0.5097	0.064*
C36	0.0773 (2)	0.22397 (13)	0.5859 (2)	0.0480 (5)
H36	0.0902	0.1754	0.5751	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0674 (11)	0.0398 (8)	0.0723 (11)	0.0032 (8)	0.0477 (10)	−0.0045 (8)
O2	0.0679 (12)	0.0406 (9)	0.0727 (11)	0.0090 (8)	0.0484 (10)	0.0052 (8)
O3	0.0489 (9)	0.0693 (11)	0.0468 (8)	0.0229 (8)	0.0329 (8)	0.0118 (7)
O4	0.0441 (9)	0.0691 (11)	0.0456 (8)	0.0075 (8)	0.0284 (7)	−0.0114 (7)
O5	0.1121 (19)	0.0656 (13)	0.1298 (19)	0.0416 (13)	0.0974 (18)	0.0511 (13)
O6	0.0801 (15)	0.0650 (13)	0.1276 (19)	−0.0250 (11)	0.0715 (14)	−0.0503 (13)
C1	0.0473 (12)	0.0584 (14)	0.0462 (12)	0.0211 (10)	0.0368 (11)	0.0146 (10)
C2	0.0748 (18)	0.0779 (19)	0.0782 (18)	0.0407 (15)	0.0640 (17)	0.0389 (15)
C3	0.081 (2)	0.161 (4)	0.080 (2)	0.077 (3)	0.064 (2)	0.080 (3)
C4	0.0517 (18)	0.217 (5)	0.0412 (15)	0.054 (3)	0.0328 (14)	0.038 (2)
C5	0.0345 (14)	0.219 (5)	0.0422 (15)	0.004 (2)	0.0201 (13)	−0.042 (2)
C6	0.0496 (17)	0.167 (4)	0.082 (2)	−0.031 (2)	0.0411 (18)	−0.083 (3)
C7	0.0424 (13)	0.080 (2)	0.0774 (18)	−0.0113 (13)	0.0403 (14)	−0.0387 (15)
C8	0.0302 (10)	0.0581 (14)	0.0470 (12)	0.0028 (9)	0.0244 (9)	−0.0147 (10)
C9	0.0329 (11)	0.0798 (15)	0.0347 (10)	0.0158 (11)	0.0230 (9)	−0.0004 (11)
C10	0.0336 (12)	0.159 (3)	0.0319 (11)	0.0234 (16)	0.0206 (10)	−0.0003 (16)
C11	0.0501 (12)	0.0401 (11)	0.0516 (12)	0.0021 (9)	0.0396 (11)	0.0009 (9)
C12	0.0329 (10)	0.0386 (10)	0.0411 (10)	−0.0010 (8)	0.0252 (9)	−0.0009 (8)
C13	0.0372 (11)	0.0491 (11)	0.0418 (10)	−0.0025 (9)	0.0269 (10)	−0.0094 (9)
C14	0.0351 (11)	0.0609 (13)	0.0352 (10)	0.0035 (9)	0.0213 (9)	−0.0013 (9)
C15	0.0341 (10)	0.0437 (11)	0.0426 (10)	0.0057 (9)	0.0257 (9)	0.0040 (9)
C16	0.0405 (11)	0.0445 (11)	0.0421 (10)	0.0030 (9)	0.0287 (9)	−0.0050 (8)
C17	0.0346 (10)	0.0504 (12)	0.0362 (10)	0.0050 (9)	0.0232 (9)	0.0013 (8)
C18	0.0355 (10)	0.0386 (11)	0.0523 (12)	0.0013 (9)	0.0283 (10)	−0.0003 (9)
C19	0.0377 (10)	0.0384 (10)	0.0410 (10)	0.0008 (8)	0.0289 (9)	0.0017 (8)
C20	0.0385 (11)	0.0489 (11)	0.0418 (10)	0.0101 (9)	0.0278 (9)	0.0092 (9)
C21	0.0400 (11)	0.0627 (13)	0.0346 (10)	0.0052 (10)	0.0247 (9)	0.0016 (9)
C22	0.0392 (11)	0.0460 (11)	0.0404 (10)	0.0016 (9)	0.0289 (9)	−0.0025 (9)
C23	0.0379 (10)	0.0450 (11)	0.0405 (10)	0.0104 (9)	0.0259 (9)	0.0054 (8)
C24	0.0350 (11)	0.0509 (12)	0.0360 (10)	0.0034 (9)	0.0241 (9)	−0.0008 (8)
C25	0.0310 (10)	0.0608 (14)	0.0350 (10)	0.0065 (9)	0.0184 (9)	−0.0036 (9)
C26	0.0390 (12)	0.0598 (14)	0.0540 (13)	0.0056 (10)	0.0281 (11)	−0.0001 (11)
C27	0.0425 (12)	0.0593 (15)	0.0600 (14)	0.0066 (11)	0.0303 (11)	−0.0098 (12)
C28	0.0370 (11)	0.0753 (16)	0.0529 (12)	−0.0033 (11)	0.0294 (11)	−0.0173 (12)
C29	0.0395 (12)	0.0713 (16)	0.0431 (12)	−0.0088 (11)	0.0248 (10)	−0.0100 (11)
C30	0.0368 (11)	0.0516 (13)	0.0411 (11)	0.0009 (9)	0.0196 (10)	−0.0073 (9)
C31	0.0428 (11)	0.0600 (14)	0.0358 (10)	0.0109 (10)	0.0280 (10)	0.0043 (9)
C32	0.0589 (15)	0.0611 (14)	0.0552 (13)	0.0054 (11)	0.0439 (13)	0.0000 (11)
C33	0.0672 (16)	0.0597 (15)	0.0581 (14)	0.0193 (13)	0.0481 (13)	0.0102 (11)
C34	0.0507 (13)	0.0771 (17)	0.0521 (12)	0.0203 (13)	0.0400 (11)	0.0176 (12)
C35	0.0514 (14)	0.0697 (16)	0.0444 (12)	0.0038 (12)	0.0336 (11)	0.0090 (11)
C36	0.0547 (13)	0.0530 (13)	0.0417 (11)	0.0106 (10)	0.0342 (11)	0.0075 (9)

Geometric parameters (Å, º) top

O1—C11	1.228 (3)	C16—H16	0.9500
O2—C18	1.230 (3)	C17—H17	0.9500
O3—C15	1.380 (2)	C18—C19	1.481 (3)
O3—C25	1.392 (3)	C19—C20	1.393 (3)
O4—C22	1.377 (2)	C19—C24	1.397 (3)
O4—C31	1.395 (3)	C20—C21	1.372 (3)
O5—C2	1.355 (4)	C20—H20	0.9500
O5—H5A	0.8400	C21—C22	1.383 (3)
O6—C7	1.348 (4)	C21—H21	0.9500
O6—H6A	0.8400	C22—C23	1.391 (3)
C1—C2	1.401 (3)	C23—C24	1.387 (3)
C1—C9	1.435 (4)	C23—H23	0.9500
C1—C11	1.485 (3)	C24—H24	0.9500
C2—C3	1.399 (5)	C25—C26	1.373 (3)
C3—C4	1.329 (6)	C25—C30	1.382 (3)
C3—H3	0.9500	C26—C27	1.387 (4)
C4—C10	1.423 (6)	C26—H26	0.9500
C4—H4	0.9500	C27—C28	1.370 (4)
C5—C6	1.364 (6)	C27—H27	0.9500
C5—C10	1.428 (6)	C28—C29	1.387 (4)
C5—H5	0.9500	C28—H28	0.9500
C6—C7	1.381 (5)	C29—C30	1.381 (3)
C6—H6	0.9500	C29—H29	0.9500
C7—C8	1.404 (3)	C30—H30	0.9500
C8—C9	1.435 (4)	C31—C32	1.372 (3)
C8—C18	1.484 (3)	C31—C36	1.376 (3)
C9—C10	1.422 (3)	C32—C33	1.383 (4)
C11—C12	1.484 (3)	C32—H32	0.9500
C12—C13	1.392 (3)	C33—C34	1.379 (4)
C12—C17	1.396 (3)	C33—H33	0.9500
C13—C14	1.375 (3)	C34—C35	1.374 (4)
C13—H13	0.9500	C34—H34	0.9500
C14—C15	1.385 (3)	C35—C36	1.390 (3)
C14—H14	0.9500	C35—H35	0.9500
C15—C16	1.383 (3)	C36—H36	0.9500
C16—C17	1.387 (3)

C15—O3—C25	119.93 (16)	O2—C18—C8	120.5 (2)
C22—O4—C31	119.97 (16)	C19—C18—C8	121.35 (18)
C2—O5—H5A	109.5	C20—C19—C24	118.61 (18)
C7—O6—H6A	109.5	C20—C19—C18	118.29 (18)
C2—C1—C9	119.7 (2)	C24—C19—C18	122.58 (18)
C2—C1—C11	115.2 (2)	C21—C20—C19	121.27 (19)
C9—C1—C11	124.8 (2)	C21—C20—H20	119.4
O5—C2—C3	117.3 (3)	C19—C20—H20	119.4
O5—C2—C1	122.7 (3)	C20—C21—C22	119.41 (19)
C3—C2—C1	120.0 (3)	C20—C21—H21	120.3
C4—C3—C2	120.9 (3)	C22—C21—H21	120.3
C4—C3—H3	119.6	O4—C22—C21	116.27 (18)
C2—C3—H3	119.6	O4—C22—C23	122.82 (18)
C3—C4—C10	121.9 (3)	C21—C22—C23	120.80 (18)
C3—C4—H4	119.1	C24—C23—C22	119.10 (19)
C10—C4—H4	119.1	C24—C23—H23	120.4
C6—C5—C10	121.7 (3)	C22—C23—H23	120.4
C6—C5—H5	119.2	C23—C24—C19	120.58 (18)
C10—C5—H5	119.2	C23—C24—H24	119.7
C5—C6—C7	120.0 (3)	C19—C24—H24	119.7
C5—C6—H6	120.0	C26—C25—C30	121.1 (2)
C7—C6—H6	120.0	C26—C25—O3	116.2 (2)
O6—C7—C6	116.1 (3)	C30—C25—O3	122.5 (2)
O6—C7—C8	122.9 (3)	C25—C26—C27	119.0 (2)
C6—C7—C8	121.0 (4)	C25—C26—H26	120.5
C7—C8—C9	119.8 (2)	C27—C26—H26	120.5
C7—C8—C18	115.2 (2)	C28—C27—C26	120.8 (2)
C9—C8—C18	124.7 (2)	C28—C27—H27	119.6
C10—C9—C8	117.7 (3)	C26—C27—H27	119.6
C10—C9—C1	117.6 (3)	C27—C28—C29	119.7 (2)
C8—C9—C1	124.71 (18)	C27—C28—H28	120.2
C9—C10—C4	119.0 (3)	C29—C28—H28	120.2
C9—C10—C5	118.9 (3)	C30—C29—C28	120.2 (2)
C4—C10—C5	122.1 (3)	C30—C29—H29	119.9
O1—C11—C12	117.7 (2)	C28—C29—H29	119.9
O1—C11—C1	120.6 (2)	C29—C30—C25	119.3 (2)
C12—C11—C1	121.13 (18)	C29—C30—H30	120.4
C13—C12—C17	118.70 (18)	C25—C30—H30	120.4
C13—C12—C11	118.15 (18)	C32—C31—C36	121.1 (2)
C17—C12—C11	122.61 (18)	C32—C31—O4	116.1 (2)
C14—C13—C12	121.21 (19)	C36—C31—O4	122.6 (2)
C14—C13—H13	119.4	C31—C32—C33	119.3 (2)
C12—C13—H13	119.4	C31—C32—H32	120.3
C13—C14—C15	119.11 (19)	C33—C32—H32	120.3
C13—C14—H14	120.4	C34—C33—C32	120.4 (2)
C15—C14—H14	120.4	C34—C33—H33	119.8
O3—C15—C16	123.03 (18)	C32—C33—H33	119.8
O3—C15—C14	115.80 (18)	C35—C34—C33	119.7 (2)
C16—C15—C14	121.08 (18)	C35—C34—H34	120.1
C15—C16—C17	119.23 (19)	C33—C34—H34	120.1
C15—C16—H16	120.4	C34—C35—C36	120.3 (2)
C17—C16—H16	120.4	C34—C35—H35	119.8
C16—C17—C12	120.47 (18)	C36—C35—H35	119.8
C16—C17—H17	119.8	C31—C36—C35	119.1 (2)
C12—C17—H17	119.8	C31—C36—H36	120.5
O2—C18—C19	117.5 (2)	C35—C36—H36	120.5

C9—C1—C2—O5	176.4 (2)	O3—C15—C16—C17	178.0 (2)
C11—C1—C2—O5	−9.4 (3)	C14—C15—C16—C17	1.6 (3)
C9—C1—C2—C3	−7.1 (3)	C15—C16—C17—C12	2.6 (3)
C11—C1—C2—C3	167.1 (2)	C13—C12—C17—C16	−3.8 (3)
O5—C2—C3—C4	175.7 (3)	C11—C12—C17—C16	167.6 (2)
C1—C2—C3—C4	−1.0 (4)	C7—C8—C18—O2	34.8 (3)
C2—C3—C4—C10	4.1 (5)	C9—C8—C18—O2	−151.6 (2)
C10—C5—C6—C7	4.3 (5)	C7—C8—C18—C19	−135.9 (2)
C5—C6—C7—O6	175.6 (3)	C9—C8—C18—C19	37.8 (3)
C5—C6—C7—C8	−1.4 (4)	O2—C18—C19—C20	26.1 (3)
O6—C7—C8—C9	176.5 (2)	C8—C18—C19—C20	−163.0 (2)
C6—C7—C8—C9	−6.7 (3)	O2—C18—C19—C24	−145.5 (2)
O6—C7—C8—C18	−9.5 (3)	C8—C18—C19—C24	25.5 (3)
C6—C7—C8—C18	167.4 (2)	C24—C19—C20—C21	0.5 (3)
C7—C8—C9—C10	11.6 (3)	C18—C19—C20—C21	−171.4 (2)
C18—C8—C9—C10	−161.8 (2)	C19—C20—C21—C22	3.6 (3)
C7—C8—C9—C1	−168.3 (2)	C31—O4—C22—C21	−146.0 (2)
C18—C8—C9—C1	18.3 (3)	C31—O4—C22—C23	37.7 (3)
C2—C1—C9—C10	11.7 (3)	C20—C21—C22—O4	178.6 (2)
C11—C1—C9—C10	−161.8 (2)	C20—C21—C22—C23	−5.0 (3)
C2—C1—C9—C8	−168.4 (2)	O4—C22—C23—C24	178.3 (2)
C11—C1—C9—C8	18.0 (3)	C21—C22—C23—C24	2.1 (3)
C8—C9—C10—C4	171.4 (2)	C22—C23—C24—C19	2.1 (3)
C1—C9—C10—C4	−8.7 (3)	C20—C19—C24—C23	−3.5 (3)
C8—C9—C10—C5	−8.7 (3)	C18—C19—C24—C23	168.1 (2)
C1—C9—C10—C5	171.2 (2)	C15—O3—C25—C26	−140.9 (2)
C3—C4—C10—C9	0.9 (4)	C15—O3—C25—C30	44.7 (3)
C3—C4—C10—C5	−178.9 (3)	C30—C25—C26—C27	−0.8 (3)
C6—C5—C10—C9	0.9 (4)	O3—C25—C26—C27	−175.3 (2)
C6—C5—C10—C4	−179.2 (3)	C25—C26—C27—C28	1.1 (4)
C2—C1—C11—O1	34.9 (3)	C26—C27—C28—C29	−0.5 (4)
C9—C1—C11—O1	−151.3 (2)	C27—C28—C29—C30	−0.3 (3)
C2—C1—C11—C12	−136.1 (2)	C28—C29—C30—C25	0.5 (3)
C9—C1—C11—C12	37.7 (3)	C26—C25—C30—C29	0.0 (3)
O1—C11—C12—C13	26.0 (3)	O3—C25—C30—C29	174.1 (2)
C1—C11—C12—C13	−162.8 (2)	C22—O4—C31—C32	−141.1 (2)
O1—C11—C12—C17	−145.5 (2)	C22—O4—C31—C36	44.7 (3)
C1—C11—C12—C17	25.8 (3)	C36—C31—C32—C33	−1.2 (3)
C17—C12—C13—C14	0.8 (3)	O4—C31—C32—C33	−175.38 (19)
C11—C12—C13—C14	−171.0 (2)	C31—C32—C33—C34	1.2 (3)
C12—C13—C14—C15	3.3 (3)	C32—C33—C34—C35	−0.7 (4)
C25—O3—C15—C16	37.3 (3)	C33—C34—C35—C36	0.2 (3)
C25—O3—C15—C14	−146.1 (2)	C32—C31—C36—C35	0.6 (3)
C13—C14—C15—O3	178.8 (2)	O4—C31—C36—C35	174.45 (19)
C13—C14—C15—C16	−4.5 (3)	C34—C35—C36—C31	−0.1 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C25—C30 and C31—C36 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1	0.84	1.83	2.560 (3)	145
O6—H6A···O2	0.84	1.88	2.563 (3)	138
C26—H26···O4ⁱ	0.95	2.48	3.377 (4)	157
C27—H27···O1ⁱ	0.95	2.51	3.269 (4)	137
C32—H32···O3ⁱⁱ	0.95	2.49	3.382 (4)	156
C33—H33···O2ⁱⁱ	0.95	2.51	3.270 (4)	137
C14—H14···Cg1ⁱⁱⁱ	0.95	2.80	3.740 (2)	171
C21—H21···Cg2^iv	0.95	2.80	3.740 (2)	171

Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x−1/2, y+1/2, z; (iii) x, −y, z+1/2; (iv) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₃₆H₂₄O₆
M_r	552.55
Crystal system, space group	Monoclinic, Cc
Temperature (K)	193
a, b, c (Å)	16.0313 (3), 18.4956 (3), 12.1238 (2)
β (°)	131.389 (1)
V (Å³)	2696.95 (9)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.60 × 0.55 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.661, 0.929
No. of measured, independent and observed [I > 2σ(I)] reflections	22236, 4868, 4527
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.096, 1.08
No. of reflections	4868
No. of parameters	382
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21
Absolute structure	Flack (1983), 2389 Friedel pairs
Absolute structure parameter	0.05 (19)

Computer programs: PROCESS-AUTO (Rigaku, 1998), Il Milione (Burla et al., 2007), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C25—C30 and C31—C36 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1	0.84	1.83	2.560 (3)	145
O6—H6A···O2	0.84	1.88	2.563 (3)	138
C26—H26···O4ⁱ	0.95	2.48	3.377 (4)	157
C27—H27···O1ⁱ	0.95	2.51	3.269 (4)	137
C32—H32···O3ⁱⁱ	0.95	2.49	3.382 (4)	156
C33—H33···O2ⁱⁱ	0.95	2.51	3.270 (4)	137
C14—H14···Cg1ⁱⁱⁱ	0.95	2.80	3.740 (2)	171
C21—H21···Cg2^iv	0.95	2.80	3.740 (2)	171

Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x−1/2, y+1/2, z; (iii) x, −y, z+1/2; (iv) x+1/2, −y+1/2, z+1/2.

Acknowledgements

The authors would like to express their gratitude to Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, for his technical advice. This work was partially supported by the Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609–613. Web of Science CrossRef CAS IUCr Journals Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Hijikata, D., Takada, T., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2902–o2903. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Okamoto, A., Hijikata, D., Sakai, N. & Yonezawa, N. (2013). Polym. J. In the press. doi:10.1038/pj.2012.135. Google Scholar
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Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914–915. Web of Science CrossRef CAS Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 69| Part 2| February 2013| Pages o208-o209

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[2,7-Dihy­dr­oxy-8-(4-phen­­oxy­benzo­yl)naphthalen-1-yl](4-phen­­oxy­phen­yl)methanone

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[2,7-Dihydroxy-8-(4-phenoxybenzoyl)naphthalen-1-yl](4-phenoxyphenyl)methanone